1-Butanol → 4-Tetradecyl-2-methylquinolin-6-ol Hydrochloride Hydrate

HRID 1720273노트

반응식

HRID 1720273 반응식
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[CH2:14](N)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(O)CCC.Cl>CO>[OH2:12].[ClH:1].[CH2:27]([C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14]

참가 물질

6

반응물 4

HCID 2631-ButanolHCID 313Hydrochloric AcidHCID 16217TetradecylamineHCID 7715204-Chloro-2-methylquinolin-6-ol

생성물 1

HCID 224179544-Tetradecyl-2-methylquinolin-6-ol Hydrochloride Hydrate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 150 mg (0.78 mmol) of 4-chloro-2-methylquinolin-6-ol, 174 mg (0.81 mmol) of n-tetradecylamine, and 5 mL of n-butanol was heated under reflux for 24 hours. Excess butanol was removed by codistillation with cyclohexane. The residue was chromatographed on 30 g of silica gel (eluent 1:9 methanol-dichloromethane) to furnish crude product. This was taken up in methanol, and the solution was treated with dry hydrogen chloride gas. The solution was evaporated under reduced pressure to give the title compound as crystalline material: m.p. 180°-183° C.

후처리

  1. temperatureunder reflux for 24 hours
  2. customExcess butanol was removed by codistillation with cyclohexane
  3. customThe residue was chromatographed on 30 g of silica gel (eluent 1:9 methanol-dichloromethane)
  4. customto furnish crude product
  5. customThe solution was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-340b3e54260d4e0587106922691e4d8e
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05506235

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